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3-substituted indole angiogenesis inhibitors

a technology of indole carbohydrazide and indole carbohydrazide, which is applied in the direction of biocide, heterocyclic compound active ingredients, drug compositions, etc., can solve the problem of not being developed

Inactive Publication Date: 2001-11-27
ABBVIE INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

In another embodiment, the instant invention provides a method of inhibiting angiogenesis in a mammal in recognized need of such treatment comprising administering to the mammal a therapeutically acceptable amount of a compound of formula (I), or a therapeutically acceptable salt thereof.

Problems solved by technology

Several angiogenesis inhibitors are currently under development for use in treating angiogenic diseases, but there are disadvantages associated with these compounds.
Fumagillin, a compound secreted by the fungus Aspergillus fumigatis fresenius, has demonstrated angioinhibitory effects, but has not been developed clinically due to the dramatic weight loss suffered by laboratory animals after prolonged exposure.

Method used

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  • 3-substituted indole angiogenesis inhibitors
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  • 3-substituted indole angiogenesis inhibitors

Examples

Experimental program
Comparison scheme
Effect test

example 1

N'-((4-methoxyphenyl)methylidene)-3-phenyl-1H-indole-2-carbohydrazide

example 1a

ethyl 2-oxo-3-phenylpropanoate

A solution of diethyl oxalate (11.15 mL, 82.1 mmol) in diethyl ether (50 mL) at -78.degree. C. was treated dropwise with 1 M benzylmagnesium chloride in diethyl ether (82 mL, 82 mmol) while maintaining an internal temperature of -60.degree. C. The mixture was stirred for 30 minutes and poured into a mixture of concentrated HCl (8 mL), ice (40 mL), and diethyl ether (50 mL). The organic phase was washed with water and brine, dried (MgSO.sub.4), filtered, and concentrated to provide 15.5 g (98%) of the desired product of sufficient purity for subsequent use.

example 1b

ethyl 3-phenyl-1H-indole-2-carboxylate

A mixture of Example 1A (7.81 g, 40.7 mmol) and phenylhydrazine (4.00 mL, 40.7 mmol) was treated with concentrated sulfuric acid (4 drops), heated to 120.degree. C. for 15 minutes, cooled to room temperature, treated with ethanol (50 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (100 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (Na.sub.2 SO.sub.4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 3.43 g (32%) of the desired product.

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Abstract

3-Substituted indole carbohydrazides having the formula ##STR1## are useful for inhibiting angiogenesis. Also disclosed are angiogenesis-inhibiting compositions and methods of inhibiting angiogenesis in a mammal.

Description

TECHNICAL FIELDThe instant invention relates to 3-substituted indole carbohydrazides which are useful for treating angiogenesis, methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.BACKGROUND OF THE INVENTIONAngiogenesis, the process by which new blood vessels are formed, is essential for normal body activities including reproduction, development, and wound repair. Although the process is not completely understood, it is believed to involve a complex interplay of molecules which regulate the growth of endothelial cells (the primary cells of capillary blood vessels). Under normal conditions, these molecules appear to maintain the microvasculature in a quiescent state (i.e., one of no capillary growth) for prolonged periods which may last for weeks or, in some cases, decades. When necessary (such as during wound repair), these same cells can undergo short bursts of growth and rapid proliferation (J. Biol. Chem. 1992, 267...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07D209/04C07D409/00C07D209/00C07D403/12C07D405/00C07D405/12C07D409/12C07D401/12C07D403/00C07D417/00C07D401/00C07D417/12A61P35/00A61P43/00
CPCC07D209/04C07D401/12C07D403/12C07D405/12C07D409/12C07D417/12A61P35/00A61P43/00
Inventor BAMAUNG, NWE Y.CRAIG, RICHARD A.KAWAI, MEGUMIWANG, JIEYI
Owner ABBVIE INC
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